I'm a wood guy first and foremost, so I'm now stepping in to the deep end.
If one were to do this on hardened steel, doesn't even that little bit of material removal for the secondary detent compromise the bit's strength? If so, it's probably not a big deal when drilling wood; but if true, I imagine it would be when resistance is higher such as drilling steel or driving hardware.
I guess my mind tells me that altering hardened steel (post hardening) is like trying to cut tempered glass (post tempering).
Just thinkin, not sayin...